WO1996018634B1 - Derives de nucleosides comportant des groupes protecteurs photolabiles - Google Patents
Derives de nucleosides comportant des groupes protecteurs photolabilesInfo
- Publication number
- WO1996018634B1 WO1996018634B1 PCT/EP1995/004976 EP9504976W WO9618634B1 WO 1996018634 B1 WO1996018634 B1 WO 1996018634B1 EP 9504976 W EP9504976 W EP 9504976W WO 9618634 B1 WO9618634 B1 WO 9618634B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- halogen
- och
- amino
- guanine
- cytosine
- Prior art date
Links
- 230000001681 protective Effects 0.000 title claims abstract 7
- 150000003833 nucleoside derivatives Chemical class 0.000 title claims abstract 3
- GFFGJBXGBJISGV-UHFFFAOYSA-N adenyl group Chemical group N1=CN=C2N=CNC2=C1N GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims abstract 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract 6
- 150000002367 halogens Chemical class 0.000 claims abstract 6
- -1 2,6-diaminopurine-9-yl Chemical group 0.000 claims abstract 5
- 229960000643 Adenine Drugs 0.000 claims abstract 4
- OPTASPLRGRRNAP-UHFFFAOYSA-N Cytosine Chemical group NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims abstract 4
- 229940104302 Cytosine Drugs 0.000 claims abstract 4
- UYTPUPDQBNUYGX-UHFFFAOYSA-N Guanine Chemical group O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims abstract 4
- RWQNBRDOKXIBIV-UHFFFAOYSA-N Thymine Chemical group CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract 4
- 125000004432 carbon atoms Chemical group C* 0.000 claims abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 4
- 229920000272 Oligonucleotide Polymers 0.000 claims abstract 3
- 229940113082 Thymine Drugs 0.000 claims abstract 2
- 229910052794 bromium Inorganic materials 0.000 claims abstract 2
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 2
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 2
- 239000002773 nucleotide Substances 0.000 claims abstract 2
- 125000003729 nucleotide group Chemical group 0.000 claims abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 2
- ACNXXUCYLYKAPB-UHFFFAOYSA-N 5-bromo-6-pyrrolidin-1-yl-1H-pyrimidine-2,4-dione Chemical compound OC1=NC(O)=C(Br)C(N2CCCC2)=N1 ACNXXUCYLYKAPB-UHFFFAOYSA-N 0.000 claims 1
- 229910004013 NO 2 Inorganic materials 0.000 claims 1
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- PWCLNQLPYQVWAB-UHFFFAOYSA-N 5-aminoimidazole-4-carboxylic acid Chemical group NC=1NC=NC=1C(O)=O PWCLNQLPYQVWAB-UHFFFAOYSA-N 0.000 abstract 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical group O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 abstract 2
- 238000000018 DNA microarray Methods 0.000 abstract 1
- 229940035893 Uracil Drugs 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 125000004430 oxygen atoms Chemical group O* 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 230000002194 synthesizing Effects 0.000 abstract 1
Abstract
La présente invention concerne des dérivés de nucléosides comportant des groupes protecteurs photolabiles, de formule générale (I) où R1 = H, NO¿2?, CN, OCH3, halogène ou alcoyle ou alcoxyalcoyle ayant de 1 à 4 atomes de C; R?2¿ = H, OCH¿3; R?3 = H, F, Cl, Br, NO¿2; R?4 = H, halogène, OCH¿3? ou un reste d'alcoyle ayant de 1 à 4 atomes de C; R?5¿ = H ou un groupe protecteur fonctionnel usuel pour l'atome d'oxygène, convenant pour la préparation d'oligonucléotides; R6 = H, OH, halogène ou XR8, avec X = 0 ou S et R8 étant un groupe protecteur usuel en chimie des nucléotides; B = adénine, cytosine, guanine, thymine, uracile, 2, 6-diaminopurin-9-yle, hypoxanthin-9-yle, 5-méthylcytosin-1-yle, 5-amino-4-amide d'acide carboxylique imidazol-1-yle ou 5-amino-4-amide d'acide carboxylique imidazol-3-yle. Dans le cas où B = adénine, cytosine ou guanine, la fonction amino primaire comporte, le cas échéant, un groupe protecteur permanent. Ces dérivés peuvent être employés pour la synthèse, commandée par la lumière, d'oligonucléotides sur une plaquette d'ADN.
Priority Applications (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP8518276A JPH11501287A (ja) | 1994-12-16 | 1995-12-15 | 光に不安定な保護基を有するヌクレオシド誘導体 |
EP95942675A EP0797580B1 (fr) | 1994-12-16 | 1995-12-15 | Derives de nucleosides comportant des groupes protecteurs photolabiles |
BR9510498-4A BR9510498A (pt) | 1994-12-16 | 1995-12-15 | Derivados de nucleosìdeos com grupos de proteção fotolábeis |
CZ19971836A CZ292296B6 (cs) | 1994-12-16 | 1995-12-15 | Deriváty nukleosidů s fotolabilními chránicími skupinami, způsob jejich přípravy a jejich použití |
DK95942675T DK0797580T3 (da) | 1994-12-16 | 1995-12-15 | Nucleosidderivater med fotolabile beskyttelsesgrupper |
AT95942675T ATE215957T1 (de) | 1994-12-16 | 1995-12-15 | Nucleosid-derivate mit photolabilen schutzgruppen |
US08/693,217 US5763599A (en) | 1994-12-16 | 1995-12-15 | Nucleoside derivatives with photolabile protective groups |
DE59510162T DE59510162D1 (de) | 1994-12-16 | 1995-12-15 | Nucleosid-derivate mit photolabilen schutzgruppen |
AU43865/96A AU692658B2 (en) | 1994-12-16 | 1995-12-15 | Nucleoside derivatives with photolabile protective groups |
HU9701821A HU215543B (hu) | 1994-12-16 | 1995-12-15 | Fényérzékeny védőcsoportot tartalmazó nukleozidszármazékok, eljárás előállításukra és alkalmazásuk |
NO972754A NO307382B1 (no) | 1994-12-16 | 1997-06-13 | Nukleosidderivater med fotolabile beskyttende grupper |
FI973643A FI973643A (fi) | 1994-12-16 | 1997-09-09 | Valonherkkiä suojausryhmiä sisältäviä nukleosidijohdoksia |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP4444996.8 | 1994-12-16 | ||
DE4444996A DE4444996A1 (de) | 1994-12-16 | 1994-12-16 | Nucleosid-Derivate mit photolabilen Schutzgruppen |
Publications (3)
Publication Number | Publication Date |
---|---|
WO1996018634A2 WO1996018634A2 (fr) | 1996-06-20 |
WO1996018634A3 WO1996018634A3 (fr) | 1996-08-22 |
WO1996018634B1 true WO1996018634B1 (fr) | 1996-09-26 |
Family
ID=6536071
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1995/004976 WO1996018634A2 (fr) | 1994-12-16 | 1995-12-15 | Derives de nucleosides comportant des groupes protecteurs photolabiles |
Country Status (17)
Country | Link |
---|---|
US (1) | US5763599A (fr) |
EP (1) | EP0797580B1 (fr) |
JP (1) | JPH11501287A (fr) |
KR (1) | KR100395290B1 (fr) |
AT (1) | ATE215957T1 (fr) |
AU (1) | AU692658B2 (fr) |
BR (1) | BR9510498A (fr) |
CA (1) | CA2207912A1 (fr) |
CZ (1) | CZ292296B6 (fr) |
DE (2) | DE4444996A1 (fr) |
DK (1) | DK0797580T3 (fr) |
ES (1) | ES2174976T3 (fr) |
FI (1) | FI973643A (fr) |
HU (1) | HU215543B (fr) |
IL (1) | IL116407A (fr) |
NO (1) | NO307382B1 (fr) |
WO (1) | WO1996018634A2 (fr) |
Families Citing this family (36)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20110028350A1 (en) * | 1995-12-15 | 2011-02-03 | Affymetrix, Inc. | Photocleavable protecting groups |
US6147205A (en) * | 1995-12-15 | 2000-11-14 | Affymetrix, Inc. | Photocleavable protecting groups and methods for their use |
WO1997041139A2 (fr) | 1996-04-17 | 1997-11-06 | Koester Hubert | Strategie combinatoire par groupes de protection pour molecules multifonctionnelles |
DE19620170A1 (de) * | 1996-05-20 | 1997-11-27 | Wolfgang Prof Dr Dr Pfleiderer | Nucleosid-Derivate mit photolabilen Schutzgruppen |
US7138384B1 (en) | 1997-08-29 | 2006-11-21 | The Regents Of The University Of California | Modulators of DNA cytosine-5 methyltransferase and methods for use thereof |
US6222030B1 (en) * | 1998-08-03 | 2001-04-24 | Agilent Technologies, Inc. | Solid phase synthesis of oligonucleotides using carbonate protecting groups and alpha-effect nucleophile deprotection |
WO2000011446A2 (fr) | 1998-08-21 | 2000-03-02 | University Of Virginia Patent Foundation | Biocapteur generateur de signaux base sur les oligonucleotides |
US6187540B1 (en) | 1998-11-09 | 2001-02-13 | Identigene, Inc. | Method of newborn identification and tracking |
DE19858440A1 (de) * | 1998-12-17 | 2000-06-21 | Deutsches Krebsforsch | Verfahren zur photolithografischen Biochip-Synthese |
EP1163251A1 (fr) | 1999-03-24 | 2001-12-19 | THE GOVERNMENT OF THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES | N-acylphosphoramidites et leur utilisation dans la synthese d'oligonucleotides |
WO2000061594A2 (fr) * | 1999-04-08 | 2000-10-19 | Deutsches Krebsforschungszentrum Stiftung des öffentlichen Rechts | Derives de nucleosides dotes de groupes protecteurs photo-instables |
DE19952113A1 (de) * | 1999-10-29 | 2001-05-03 | Nigu Chemie Gmbh | Nucleosid-Derivate mit photolabilen Schutzgruppen |
EP1176151B1 (fr) * | 2000-07-28 | 2014-08-20 | Agilent Technologies, Inc. | Synthèse des polynucléotides utilisant la chimie combinée d'oxidation et de protection |
CA2421732A1 (fr) * | 2000-09-11 | 2002-03-14 | Affymetrix, Inc. | Groupes de protection photoclivables |
DE10105077A1 (de) * | 2001-02-05 | 2002-08-08 | Febit Ferrarius Biotech Gmbh | Hybrid-Schutzgruppe |
DE10105079A1 (de) * | 2001-02-05 | 2002-08-08 | Febit Ferrarius Biotech Gmbh | Fotolabile Schutzgruppen für die Synthese von Biopolymeren |
EP1401851B8 (fr) * | 2001-07-03 | 2008-09-10 | febit holding GmbH | Groupes protecteurs separes en deux etapes pour la synthese de biopolymeres |
DE10152147A1 (de) * | 2001-10-25 | 2003-05-15 | Chemogenix Gmbh | Verfahren zum Aufbringen von Nukleosiden und/oder Nukleotiden auf funktionalisierten Oberflächen sowie Verfahren zur Bestimmung von Kopplungsausbeuten bei der Synthese von Nukleotiden |
DE10156467A1 (de) * | 2001-11-16 | 2003-06-05 | Micronas Gmbh | Träger zur Synthese sowie Verfahren zur Herstellung von Biopolymeren |
WO2003048179A2 (fr) * | 2001-12-03 | 2003-06-12 | The Government Of The United States Of America, Represented By The Secretary Of The Department Of Health And Human Services | Groupes protecteurs hydroxyle thermolabiles et procedes permettant de les utiliser |
EP1480927B1 (fr) | 2002-03-04 | 2012-12-26 | Universität Konstanz | Procede de clivage de groupes fonctionnels labiles a partir de composes chimiques |
DE10209203A1 (de) | 2002-03-04 | 2003-09-25 | Ulrich Steiner | Verfahren zur Abspaltung von labilen funktionellen Gruppen aus chemischen Verbindungen |
AU2003290117A1 (en) * | 2002-12-23 | 2004-07-22 | Febit Biotech Gmbh | Photoactivatable two-stage protective groups for the synthesis of biopolymers |
US20040157220A1 (en) | 2003-02-10 | 2004-08-12 | Purnima Kurnool | Methods and apparatus for sample tracking |
US7759513B2 (en) * | 2003-02-21 | 2010-07-20 | Nigu Chemie Gmbh | Photolabile protective groups for improved processes to prepare oligonucleotide arrays |
DE10315772A1 (de) * | 2003-04-07 | 2004-11-04 | Ulrich Prof. Dr. Steiner | Chemische Verbindung und Verfahren für den intramolekularen Energietransfer zur Abspaltung von labilen funktionellen Gruppen aus chemischen Verbindungen |
US7612197B2 (en) * | 2003-05-09 | 2009-11-03 | The United States of America as repesented by the Secretary of the Department of Health and Human Services | Thermolabile hydroxyl protecting groups and methods of use |
DE102004019098A1 (de) * | 2004-04-20 | 2005-11-10 | Chemogenix Gmbh | Photolabile Schutzgruppen |
US9809824B2 (en) * | 2004-12-13 | 2017-11-07 | The United States Of America, Represented By The Secretary, Department Of Health And Human Services | CpG oligonucleotide prodrugs, compositions thereof and associated therapeutic methods |
US7547775B2 (en) | 2004-12-31 | 2009-06-16 | Affymetrix, Inc. | Parallel preparation of high fidelity probes in an array format |
US8338093B2 (en) * | 2004-12-31 | 2012-12-25 | Affymetrix, Inc. | Primer array synthesis and validation |
US8343710B1 (en) | 2005-03-11 | 2013-01-01 | The Regents Of The University Of Colorado, A Body Corporate | Photodegradable groups for tunable polymeric materials |
US9180196B2 (en) | 2005-03-11 | 2015-11-10 | The Regents Of The University Of Colorado, A Body Corporate | Photodegradable groups for tunable polymeric materials |
WO2012102616A1 (fr) | 2011-01-28 | 2012-08-02 | Flexgen B.V. | Polynucléotides hétérodirectionnels |
US9139874B2 (en) | 2011-07-07 | 2015-09-22 | Life Technologies Corporation | Bi-directional sequencing compositions and methods |
US9745618B2 (en) | 2014-11-19 | 2017-08-29 | Roche Molecular Systems, Inc. | Photoblocked probes and methods for sequential detection of nucleic acids |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU5449094A (en) * | 1992-11-02 | 1994-05-24 | Affymax Technologies N.V. | Novel photoreactive protecting groups |
-
1994
- 1994-12-16 DE DE4444996A patent/DE4444996A1/de not_active Withdrawn
-
1995
- 1995-12-15 EP EP95942675A patent/EP0797580B1/fr not_active Expired - Lifetime
- 1995-12-15 US US08/693,217 patent/US5763599A/en not_active Expired - Lifetime
- 1995-12-15 JP JP8518276A patent/JPH11501287A/ja not_active Ceased
- 1995-12-15 CA CA002207912A patent/CA2207912A1/fr not_active Abandoned
- 1995-12-15 AU AU43865/96A patent/AU692658B2/en not_active Ceased
- 1995-12-15 DE DE59510162T patent/DE59510162D1/de not_active Expired - Lifetime
- 1995-12-15 IL IL11640795A patent/IL116407A/en not_active IP Right Cessation
- 1995-12-15 KR KR1019970704039A patent/KR100395290B1/ko not_active IP Right Cessation
- 1995-12-15 AT AT95942675T patent/ATE215957T1/de not_active IP Right Cessation
- 1995-12-15 ES ES95942675T patent/ES2174976T3/es not_active Expired - Lifetime
- 1995-12-15 DK DK95942675T patent/DK0797580T3/da active
- 1995-12-15 BR BR9510498-4A patent/BR9510498A/pt not_active Application Discontinuation
- 1995-12-15 WO PCT/EP1995/004976 patent/WO1996018634A2/fr active IP Right Grant
- 1995-12-15 CZ CZ19971836A patent/CZ292296B6/cs not_active IP Right Cessation
- 1995-12-15 HU HU9701821A patent/HU215543B/hu not_active IP Right Cessation
-
1997
- 1997-06-13 NO NO972754A patent/NO307382B1/no not_active IP Right Cessation
- 1997-09-09 FI FI973643A patent/FI973643A/fi not_active IP Right Cessation
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